CN103275515B - Orange naphtocyclinon dye and preparation method thereof - Google Patents
Orange naphtocyclinon dye and preparation method thereof Download PDFInfo
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- CN103275515B CN103275515B CN201310244418.2A CN201310244418A CN103275515B CN 103275515 B CN103275515 B CN 103275515B CN 201310244418 A CN201310244418 A CN 201310244418A CN 103275515 B CN103275515 B CN 103275515B
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- Prior art keywords
- orange
- dye
- naphtocyclinon
- diaminonaphthalene
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 claims abstract description 14
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000000975 dye Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000001048 orange dye Substances 0.000 claims description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical class CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 5
- 239000012065 filter cake Substances 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000009413 insulation Methods 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 abstract description 8
- 229920000728 polyester Polymers 0.000 abstract description 8
- 239000004793 Polystyrene Substances 0.000 abstract description 7
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 abstract description 7
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 abstract description 7
- 229920006351 engineering plastic Polymers 0.000 abstract description 7
- 229920000515 polycarbonate Polymers 0.000 abstract description 5
- 229920002223 polystyrene Polymers 0.000 abstract description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006482 condensation reaction Methods 0.000 abstract description 3
- 238000004043 dyeing Methods 0.000 abstract description 3
- 239000000835 fiber Substances 0.000 abstract description 3
- 238000009987 spinning Methods 0.000 abstract description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- WGBDKLPQUUXFGH-UHFFFAOYSA-N 4-methylnaphthalene-1,8-diamine Chemical group C1=CC=C2C(C)=CC=C(N)C2=C1N WGBDKLPQUUXFGH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 239000000992 solvent dye Substances 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229920004935 Trevira® Polymers 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 239000012994 photoredox catalyst Substances 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- YZSSZDOBKJTOAX-UHFFFAOYSA-N CC(C=CC(C12)N)=C1C=CC=C2N Chemical compound CC(C=CC(C12)N)=C1C=CC=C2N YZSSZDOBKJTOAX-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1c(*=O)cccc1 Chemical compound Cc1c(*=O)cccc1 0.000 description 1
- PWWJWMYGJNYQMP-UHFFFAOYSA-N Cc1ccc2N=C(c(cccc3)c3C3=O)N3c3cccc1c23 Chemical compound Cc1ccc2N=C(c(cccc3)c3C3=O)N3c3cccc1c23 PWWJWMYGJNYQMP-UHFFFAOYSA-N 0.000 description 1
- -1 DMS Chemical compound 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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- Artificial Filaments (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to orange naphtocyclinon dye and a preparation method thereof. The orange naphtocyclinon dye has a formula shown in formula I, wherein R is H or CH3. The dye is obtained by condensation reaction of 1,8-diaminonaphthalene or substituted 1,8-diaminonaphthalene and phthalic anhydride with a catalyst. The orange naphtocyclinon dye has single component and high purity, is mainly used for dyeing engineering plastics of polystyrene, ABS (Acrylonitrile Butadiene Styrene), polycarbonate, polyester and the like, as well as dyeing polyester fibers before spinning, and has the characteristics of bright color, high transparency, goodness and fastness in all capacities and the like.
Description
Technical field
The present invention relates to a kind of dye well its preparation method, be specifically related to a kind ofly spin front painted orange Naphtocyclinon dye well its preparation method for the painted and polyester fiber of engineering plastics.
Background technology
Solvent dye is the dedicated dye of the engineering plastics such as polystyrene, ABS, polycarbonate, polyester, and it has the advantages such as lovely luster, transparency is high, application performance is good, and part solvent dye is also to spin front painted important kind for polyester fiber.
Along with all types of plastic, the particularly high speed development of engineering plastics, to the thermotolerance of dyestuff, light permanency, coloured light vividness, the indexs such as transparency have more and more higher requirement, meanwhile, along with the regulation of Green Product theory more and more stricter and energy-conserving and environment-protective is rooted in the hearts of the people day by day, trevira spin the front painted increasing importance that demonstrates.The dyestuff with excellent properties and environment-friendly quality index is the essential condition that meets these requirements.
Disclosed compound of the present invention is with through being studied widely, for example prior art (Supramolecular Chemistry, 18 ((8), 605-613; 2006) Naphtocyclinon (formula II) in the time that R is H of the present invention is disclosed, and its preparation method is disclosed under existing at 1N-imidazoles, by 1,8-diaminonaphthalene and phthalic anhydride pass through heating in THF, carry out condensation reaction, but prior art does not disclose this compounds of the present invention as a kind of orange dye, painted for engineering plastics such as polystyrene, ABS, polycarbonate, polyester.
Summary of the invention
The object of this invention is to provide a kind of highly purified orange dye of single structure, can be used for the dyeing of the engineering plastics such as polystyrene, ABS, polycarbonate, polyester, also can be used for spinning of trevira front painted, have the features such as lovely luster, high, the every fastness of transparency be good, application performance is very good.
For realizing object of the present invention, technical scheme of the present invention is:
A kind of orange Naphtocyclinon dyestuff, it has as shown in the formula the structural formula shown in I:
Wherein, R is H or CH
3.
In a preferred embodiment of the present invention, shown in dyestuff just like Formula Il I, or the structural formula of formula IV, or both mixtures:
Another object of the present invention is to provide a kind of preparation method of orange Naphtocyclinon dyestuff, and the method comprises following processing step:
(1) in organic solvent, under catalyzer exists, by 1,8-diaminonaphthalene or be with substituently 1,8-diaminonaphthalene and phthalic anhydride carry out condensation reaction, and temperature of reaction is 100-160 DEG C, and the reaction times is 2-5 hour, and wherein said substituting group is methyl;
(2) reaction solution of step (1) gained is cooled to 30-45 DEG C, filters, gained filter cake organic solvent washing, then wash, then dry.
In a preferred embodiment of the present invention, in step (1), 1,8-diaminonaphthalene or be with substituently 1, the mol ratio of 8-diaminonaphthalene and phthalic anhydride is 1: 1.05-1.3,1,8-diaminonaphthalene or be with substituently 1, the mol ratio of 8-diaminonaphthalene and catalyzer is 1: 0.04-0.08.
In a preferred embodiment of the present invention, in step (1), to be describedly with substituently 1,8-diaminonaphthalene is 1,8 diamino-4-methylnaphthalene.
In a preferred embodiment of the present invention, in step (1), described catalyzer is one or more the mixture in pyridine, quinoline or piperidines.
In a preferred embodiment of the present invention, in step (1) and (2), described organic solvent is one or more the mixture in ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol ethyl ether, butyl glycol ether, DMF, DMS, dimethylbenzene or oil of mirbane.
In a preferred embodiment of the present invention, step (2) also comprises, before 30-45 DEG C, first described reaction solution is cooled to 70-90 DEG C, then adds water wherein the reaction solution of gained is cooled to.
The remnants that the toxic substances such as heavy metal, aromatic amine, many Benzene Chloride, polychlorobiphenyl all do not detected in gained dyestuff of the present invention are very products for environment-friendly type; Can be widely used in polystyrene as a kind of solvent dye, ABS, polycarbonate, the engineering plastics such as polyester painted, there is good thermotolerance, light permanency, the application performances such as transparency, and in its preparation method, each step is simple to operate, and yield is high, and solvent is recyclable recycling all.
Embodiment
In order to implement better the present invention, now enumerate following embodiment, the present invention is further illustrated, but these embodiment are not limitations of the present invention.
Embodiment 1
(1) being equipped with in the four-hole boiling flask of thermometer, agitator, water trap and prolong, add 7.2 gram 1,8 diaminonaphthalenes (0.045 mole), 7 grams of phthalic anhydrides (0.047 mole), 250 milliliters of ethylene glycol ethyl ethers and 0.2 gram of pyridine, stir and be warming up to 140 DEG C, insulation reaction 3 hours, after testing, 1,8 diaminonaphthalene reaction is complete;
(2) step (1) gained reaction solution is stirred and is cooled to 40 DEG C, filter, 100 milliliters of washing with alcohol for filter cake, then wash with water, dry, obtain 11 grams of orange dyes, yield is 93%, purity is 99.2%.
In step in the present embodiment (2), the reaction solution ethylene glycol ethyl ether in the filtrate of gained and the equal recycling of ethanol of washing use after filtration.
The analytical data of this product is as follows:
H1-NMR(DMSO-d
6):δ(ppm)7.39～7.56(m,5H),7.71～7.80(m,2H),8.01(d,1H),8.23(d,1H),8.46(d,1H).
m/e=271.1(M+H+)。
Embodiment 2
(1) being equipped with in the four-hole boiling flask of thermometer, agitator, water trap and prolong, add 7.2 gram 1,8 diaminonaphthalenes (0.045 mole), 7 grams of phthalic anhydrides (0.047 mole), 0.5 gram of quinoline and 250 milliliters of DMF, stir and be warming up to 130 DEG C, insulation reaction 5 hours, after testing, 1,8 diaminonaphthalene reaction is complete;
(2) while being cooled to 90 DEG C to step (1) gained reaction solution, adding wherein 50 ml waters, then it stirring is cooled to 30 DEG C, filter, 100 milliliters of washing with alcohol for filter cake, then wash, dry, obtain 10.8 grams of orange dyes, yield 90%, purity is 99.5%.
In step in the present embodiment (2), the reaction solution DMF in the filtrate of gained and the equal recycling of ethanol of washing use after filtration.
It is the same with the product of embodiment 1 that this product detects through thin-layer chromatography.
Embodiment 3
(1) in 500 milliliters of pressure-vessels that thermometer, agitator are housed, add 7.2 gram 1,8 diamino-4-methylnaphthalene (0.045 mole), 7 grams of phthalic anhydrides (0.047 mole), 0.4 gram of piperidines, 250 milliliters of dimethylbenzene, stirring is warming up to 140 DEG C, insulation reaction 3 hours, after testing, the reaction of 1,8 diamino-4-methylnaphthalene is complete; ;
(2) step (1) gained reaction solution is stirred and is cooled to 40 DEG C, filter 100 milliliters of washing with alcohol for filter cake, wash with water again, dry, obtain 11 grams of orange dyes, yield is 92%, and it is two kinds of materials that product detects through thin-layer chromatography, and total purity of two kinds of materials is 99.1%.
In step in the present embodiment (2), the reaction solution dimethylbenzene in the filtrate of gained and the equal recycling of ethanol of washing use after filtration.
Two kinds of materials of gained are after separating, and its analytical data is as follows respectively:
Product 1
H
1-NMR(DMSO-d6):δ(ppm)2.70(s，3H),7.41～7.61(m,6H),7.70-7.84(m,2H),8.10(d,1H).
m/e=285.0(M+H
+)。
Product 2
H
1-NMR(DMSO-d6):δ(ppm)2.76(s，3H),7.43～7.60(m,5H),7.72-7.90(m,2H),8.96(d,1H),8.15(d,1H).
m/e=285.1(M+H
+)。
The yellow dyes of by ordinary method being prepared by embodiment 1 and embodiment 2 to gained is during for the different dying polymers such as PET, PC, PMMA, and its performance is as shown in table 1:
Table 1
| Polymkeric substance title | Dyestuff % | Titanium dioxide % | Heat-resisting DEG C | Resistance to migration | Fast light | Weather-proof |
| PET | 0.02 | ? | 300 | 5 | 8 | 4-5 |
| PC | 0.05 | ? | 360 | 5 | 8 | 4 |
| PMMA | 0.05 | ? | 300 | 5 | 7-8 | 4-5 |
| PS | 0.05 | ? | 300 | 4 | 8 | ? |
| PS | 0.05 | 1.0 | 300 | 4 | 7 | ? |
| ABS | 0.10 | 1.0 | 280 | 4.8 | 7 | ? |
| HIPS | 0.10 | 0.5 | 300 | 3-4 | 7 | ? |
The yellow dyes of by ordinary method being prepared by embodiment 3 to gained is during for the different dying polymers such as PET, PC, PMMA, and its performance is as shown in table 2:
Table 2
Can find out that from table 1 and 2 dyestuff of the present invention, during for different polymkeric substance, has good thermotolerance, resistance to migration, fast light and weather resistance.
Claims (1)
1. a preparation method for orange Naphtocyclinon dyestuff, is characterized in that,
(1) being equipped with in the four-hole boiling flask of thermometer, agitator, water trap and prolong, add 7.2 gram 1,8-diaminonaphthalene, 7 grams of phthalic anhydrides, 250 milliliters of ethylene glycol ethyl ethers and 0.2 gram of pyridine, stir and be warming up to 140 DEG C, insulation reaction 3 hours, after testing, the reaction of 1,8-diaminonaphthalene is complete;
(2) step (1) gained reaction solution is stirred and is cooled to 40 DEG C, filter, 100 milliliters of washing with alcohol for filter cake, then wash with water, dry, obtain 11 grams of orange dyes, yield is 93%, purity is 99.2%;
In step (2), the reaction solution ethylene glycol ethyl ether in the filtrate of gained and the equal recycling of ethanol of washing use after filtration.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201310244418.2A CN103275515B (en) | 2013-06-18 | 2013-06-18 | Orange naphtocyclinon dye and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310244418.2A CN103275515B (en) | 2013-06-18 | 2013-06-18 | Orange naphtocyclinon dye and preparation method thereof |
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| Publication Number | Publication Date |
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| CN103275515A CN103275515A (en) | 2013-09-04 |
| CN103275515B true CN103275515B (en) | 2014-10-29 |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109762362A (en) * | 2019-01-22 | 2019-05-17 | 南通龙翔新材料科技股份有限公司 | The preparation method of pyrene ketones solvent dyestuff |
| CN112592603A (en) * | 2020-12-22 | 2021-04-02 | 安徽清科瑞洁新材料有限公司 | Green method for preparing solvent orange 60 with low pollution |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1379064A (en) * | 2001-03-29 | 2002-11-13 | 拜尔公司 | New crystal shape of dyestuff peri-ketone |
| RU2303614C1 (en) * | 2006-06-01 | 2007-07-27 | Государственное образовательное учреждение высшего профессионального образования "Московский государственный текстильный университет им. А.Н. Косыгина" | Process for production of heat-resistant perinone dyes |
| WO2009070802A1 (en) * | 2007-11-30 | 2009-06-04 | Mayan Pigments, Inc. | Hybrid pigments with coupling agents |
| CN101565556A (en) * | 2009-03-23 | 2009-10-28 | 南通龙翔化工有限公司 | Preparation method of solvent orange 60 |
| CN102421855A (en) * | 2009-04-22 | 2012-04-18 | 德司达染料德国有限责任公司 | Dyes for polymer coloration, their preparation and their use |
| CN102483478A (en) * | 2009-07-06 | 2012-05-30 | 奥斯兰姆奥普托半导体有限责任公司 | Composition for producing a filter material for radiation, method for producing a composition for a filter material, material for filtering radiation and optoelectronic component comprising said material |
-
2013
- 2013-06-18 CN CN201310244418.2A patent/CN103275515B/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1379064A (en) * | 2001-03-29 | 2002-11-13 | 拜尔公司 | New crystal shape of dyestuff peri-ketone |
| RU2303614C1 (en) * | 2006-06-01 | 2007-07-27 | Государственное образовательное учреждение высшего профессионального образования "Московский государственный текстильный университет им. А.Н. Косыгина" | Process for production of heat-resistant perinone dyes |
| WO2009070802A1 (en) * | 2007-11-30 | 2009-06-04 | Mayan Pigments, Inc. | Hybrid pigments with coupling agents |
| CN101565556A (en) * | 2009-03-23 | 2009-10-28 | 南通龙翔化工有限公司 | Preparation method of solvent orange 60 |
| CN102421855A (en) * | 2009-04-22 | 2012-04-18 | 德司达染料德国有限责任公司 | Dyes for polymer coloration, their preparation and their use |
| CN102483478A (en) * | 2009-07-06 | 2012-05-30 | 奥斯兰姆奥普托半导体有限责任公司 | Composition for producing a filter material for radiation, method for producing a composition for a filter material, material for filtering radiation and optoelectronic component comprising said material |
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